Sales Director
Sales & Business Development
Remote
Posted on Aug 11, 2026
About Discover Dollar
Discover Dollar helps large enterprises recover lost profit through AP recovery audits, contract compliance reviews, and profit leakage prevention. We work with major retail, manufacturing, CPG, healthcare, and insurance organizations including Target, ABInBev, Carrier, Canadian Tire, etc. to find and recover money that falls through the cracks of complex procure-to-pay processes.
The Role
We're looking for a Sales Director to scale our existing sales team and drive revenue growth across both direct enterprise sales and partnership-led channels. This is a player-coach role: you'll manage and develop a team of SDRs while staying close enough to the pipeline to unblock deals, shape strategy, and represent Discover Dollar in front of senior enterprise stakeholders (CFO, VP Finance, Controller, Head of AP).
You'll report directly into leadership and have real influence over how we scale go-to-market.
What You'll Do
- Lead and scale the team - Manage, coach, and grow a team of sales reps/SDRs; build repeatable processes for pipeline management, forecasting, and deal reviews.
- Own direct enterprise sales - Drive new logo acquisition and expansion within existing accounts, engaging CFOs, VPs of Finance, Controllers, and Heads of AP.
- Build and manage the partnership motion - Work alongside our partnerships team to convert channel relationships with BPO, ERP/SI, and advisory firms (e.g. benchmarking and strategic advisory partners) into qualified pipeline and closed revenue.
- Own the number - Be accountable for team quota, accurate forecasting, and pipeline health; report regularly to leadership on performance, blockers, and course corrections.
- Refine the GTM motion - Bring structure to messaging, qualification criteria, and deal stages as we drive toward a repeatable, team-driven model.
- Represent Discover Dollar externally - Lead executive-level conversations, present findings and value propositions to senior enterprise stakeholders, and negotiate contract terms.
- Collaborate cross-functionally - Work closely with audit, product, and marketing teams to ensure sales commitments align with delivery capability, and that market feedback shapes product and content strategy.
What we're looking for
- 10-20 years of B2B sales experience, with at least 3-5 years in a sales leadership/management role scaling a team (not just an IC background).
- Proven track record selling into enterprise accounts in the US and Canada market. Experience with CFO/Finance/AP stakeholders is a strong plus, especially in cost recovery, audit, procurement, fintech, or adjacent B2B SaaS/services categories.
- Experience running both direct sales and partner/channel motions. You understand how to build pipeline through partnerships (BPO, ERP/SI, advisory) in addition to direct outbound and inbound.
- Demonstrated ability to build sales processes from a relatively early stage (pipeline hygiene, forecasting discipline, coaching frameworks) rather than just operating inside an existing mature system.
- Strong executive presence; comfortable being the face of the company in high-stakes conversations with senior finance and procurement leaders.
- Data-driven approach to pipeline and team management; comfortable owning and defending a number.
- Excellent written and verbal communication; ability to translate complex value propositions (financial recovery, ROI, compliance risk) into crisp, executive-ready narratives.
Nice to Have
- Experience selling audit, compliance, cost-recovery, or fintech/SaaS solutions into Fortune 1000 accounts.
- Familiarity with partnership/channel GTM models (referral, co-sell, contingency-based).
- Experience scaling a sales team from single digits into a larger, structured org.
- Exposure to selling both services-led and SaaS-led offerings in parallel.
What We Offer
- A high-ownership role with direct influence on GTM strategy, not just execution.
- Direct access to founders and leadership; fast decision cycles.
- Competitive base + uncapped variable compensation tied to team and individual performance.
- The opportunity to build a scaled sales function from the ground up at a fast-growing company already working with marquee enterprise clients.
